Mental models can affect people’s actions and have the capacity to affect how people achieve organizational outcomes. An ethnographic complexity-based inquiry into the mental models of staff and management about work practices was undertaken within a not-for-profit organization. Interviews were conducted to uncover the mental models held by management and staff about actual work practices and ideal work practices. A comparison of the individual mental models revealed that individuals in the organization were in a state of chaotic edge thinking, where everything is perceived as a threat, procedures are formed to control, and people are reacting radically. This was a result of the miscommunication between members of the organization and an environment characterized by a negative phrase space. It is suggested that the identification of individual mental models about work practices is beneficial for knowing how a person’s actions are influenced, and in this case, why work practices failed.